(5-Acetylthiophen-2-yl)boronic acid → HCID 86696381, compound

HRID 870679Notes

Reaction equation

HRID 870679 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]3[CH3:21])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:22]([C:25]1[S:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:24])[CH3:23]>>[CH3:21][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[CH2:14][CH2:13][CH2:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:28]3[S:29][C:25]([C:22](=[O:24])[CH3:23])=[CH:26][CH:27]=3)=[CH:3][N:4]=2)[N:7]=1

Participants

3

Reactant 2

HCID 4143377(5-Acetylthiophen-2-yl)boronic acidHCID 86696382HCID 86696382, compound

Product 1

HCID 86696381HCID 86696381, compoundYield 71%

Procedure

The reaction of 3-bromo-N-(3-(2-methylpiperidin-1-yl)propyl)imidazo[1,2-b]pyridazin-6-amine with (5-acetylthiophen-2-yl)boronic acid, under the Suzuki coupling condition described in example 5.6.19, afforded the desired compound in 71% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34 (d, J=6.57 Hz, 3H) 1.45-1.59 (m, 1H) 1.67-1.96 (m, 5H) 2.13-2.31 (m, 2H) 2.60 (s, 3H) 2.74 (dd, J=10.86, 4.80 Hz, 1H) 2.83-2.95 (m, 1H) 3.11 (br. s., 1H) 3.17-3.31 (m, 1H) 3.34-3.46 (m, 1H) 3.53-3.72 (m, 2H) 6.72 (d, J=9.85 Hz, 1H) 7.56 (d, J=4.04 Hz, 1H) 7.64-7.73 (m, 2H) 7.94 (s, 1H); LRMS (ESI) m/e 398.0 [(M+H)+, calcd for C21H27N5OS 397.0].

Sources & evidence

ORD record
ord-c782b144bfe64a19a3cc7d00e6e3e72b
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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